Sodium Hydroxide → HCID 67220457, compound

HRID 1258459Notes

Reaction equation

O[C:2]1[C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[C:9]([CH3:11])=[N:10][C:6]=2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:3]=1[CH2:20][CH2:21][CH:22]([OH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[Na+]>P(=O)(O)(O)O>[CH3:15][O:14][CH2:13][CH2:12][N:8]1[C:7]2[C:2]3[O:29][CH:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:21][CH2:20][C:3]=3[C:4]([C:16]([O:18][CH3:19])=[O:17])=[CH:5][C:6]=2[N:10]=[C:9]1[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of methyl 7-hydroxy-6-(3-hydroxy-3-phenylpropyl)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylate (2.00 g, 5.01 mmol, Step 10) in 85% phosphoric acid (40 mL) was stirred at 80° C. for 20 minutes. After cooling to room temperature, the mixture was poured onto ice-water (300 mL), and the solution was neutralized by 10 N sodium hydroxide aqueous solution. The aqueous layer was extracted with dichloromethane. The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (gradient elution from ethyl acetate only to 20:1) to afford the title compound as a pale brown solid (1.47 g, 77%).

Workup

temperatureAfter cooling to room temperature
additionthe mixture was poured onto ice-water (300 mL)
extractionThe aqueous layer was extracted with dichloromethane
dry with materialThe combined organic layer was dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate/methanol (
washgradient elution from ethyl acetate only to 20:1)

Sources & evidence

ORD record: ord-99f7527e47184061a3848b9756e839d2
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466166B2

Reaction notes

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